The (Not-So) Secret History of Hunter S. Thompson's The Rum Diary

Thompson's "Long-Lost Novel" has finally been adapted for the big screen, starring (who else?) Johnny Depp. But the book itself was decades in the making, too. Discover the unknown story of the rebel New Journalist's journey into fiction

In Hunter Thompson's legendary pantheon of villainous scum, magazine editors placed somewhere between his creditors and Richard Nixon. Even in 1961, a few years before he first reached literary and journalistic fame with his 1966 book, Hell's Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gangs, few (least of all this publication, which had rejected some of his early short stories out of hand) escaped his censure:

At the moment I'm working on a novel called > The Rum Diary, which should be finished by late summer. If you would care to deal with it, by all means let me know. It will be a whomping thing and will undoubtedly draw poor comment from > Gentlemen's Quarterly, Pop, One, Ebony, and a good many others. At any rate, please let me hear from you.

This, he wrote in a letter to Sterling Lord, then the "dean" of New York literary agents. His next correspondence with Lord, after he refused to take Thompson on as a client, was somewhat less cordial:

Here's the 20 cents it cost you to send the damn [short stories] back. I don't want to feel that I owe you anything, because when I see you I intend to cave in your face and scatter your teeth all over Fifth Avenue.

Literary agents then perhaps moved up a place on his sliding scale.

These instances illuminate for us two things that even die-hard Thompson fans either may not know, or would rather ignore: first, that the young Hunter wanted, more than anything else, to be a fiction writer in the manner of Hemingway and Fitzgerald. Secondly, he was not a very good one. After much failure in getting his short stories (and a largely unknown first novel, Prince Jellyfish, deemed forgettable by his own admission) published, The Rum Diary—first "finished" in 1962—was meant to be his The Sun Also Rises. It would not be published until 1998.

Why the delay? And why publish it in the late '90s, so far from the Fear and Loathing days of the late '60s and 1970s, when the Thompson character was so transcendent and his viewpoint so vital? The short, uninteresting answer to the second question is that he needed money. (Thompson always "needed" money—or at least, made an entertaining meal of pretending to. Terry Gilliam's adaptation of Fear and Loathing in Las Vegas starring Johnny Depp and Benicio Del Toro, along with a paperback re-release of the book, were released that same year, so the proverbial iron was hot for striking.) Answering the first question is more complicated, but doing so produces an indelible picture of a young writer—recognizable more by the naiveté shared by almost all young writers than by the acerbic wit of a self-styled Doctor of Journalism—searching desperately for the right voice with which to speak, and being just on the verge of finding it.

Billed as "the long lost novel" upon its release, The Rum Diary is narrated by a young journalist named Paul Kemp who leaves New York for Puerto Rico and a job with the fictional San Juan Daily News, an English-language publication staffed by jocular degenerates, talented schemers, and other writers that he finds, upon arrival, is not long for this world. The Young Journalist Named Hunter Thompson also left New York for Puerto Rico in 1960, hoping to find work at the San Juan Star as their sports editor. His letter to publisher William Dorvillier is "instructive" of the kind of writer he fancied himself:

Dear Sir,>

I hear you need a sports editor. If true, perhaps we can work something out. The job interests me for two reasons: the Caribbean location, and the fact that it's a new paper. Salary would be entirely secondary, as it definitely would not be here in our great rotarian democracy...As for the quality of my work, I'd be either the best or the worst sports editor you could get. I'd make great demands on the photographers, insist on laying out my own pages, write a column that might make some readers strain their intellects, and generally make every effort to produce what I considered the perfect sports section. If you're looking for an easy-going hack, then I am not your man.

He continues:

Having been a sportswriter, sports editor, editorial trainee, and reporter—in that order—I have given up on American journalism. The decline of the American press has long been obvious, and my time is too valuable to waste in an effort to supply the "man in the street" with his daily quote of clichés, gossip, and erotic tripe. There is another concept of journalism, which you may or may not be familiar with. It's engraved on a bronze plaque on the southeast corner of the Times Tower in New York City.

His was not a successful application. The managing editor of the paper, William Kennedy (who would go on to win the 1984 Pulitzer Prize for fiction for Ironweed), kindly responded that their publisher was a Rotarian, that their staff was—like Thompson—full of reporters also writing novels, and that perhaps he should get back to writing his. Thompson, with the red mist of rejection descending but also sensing a worthy opponent, fired off this note, entirely in lowercase:

your letter was cute, my friend, and your interpretation of my letter was beautifully typical of the cretin-intellect responsible for the dry-rot of the american press. but don't think that lack of an invitation from you will keep me from getting down that way, and when i do remind me to first kick your teeth in and then jam a bronze plaque far into your small intestine.

give my best to your "literary" staff and your rotarian publisher. if they're half as cute as you are, your paper will be a whomping success.

Thompson eventually found a sportswriting gig with a glorified English-language newsletter called El Sportivo that existed essentially to promote bowling in Puerto Rico while giving bowlers kicks by seeing their name in print. (He and Kennedy became fast friends and kept a lively correspondence that lasted the rest of Thompson's days.) Thompson began The Rum Diary while there, living a life very much like that of his protagonist: early-morning ocean swims, mid-days full of freelance assignments ranging from cock-fighting features to writing travel brochure copy, afternoons and late evenings spent smoking pipes and drinking lustily with other itinerant souls. "Nothing but water, rum, and sun," he wrote in a letter to—yes—the beautiful blonde who soon came to live with him, Sandy Conklin (who later became his first wife and the mother of his son, Juan Fitzgerald). All of this appears in one form or another in the novel. Art did not imitate life so much as admire it boozily in the mirror.

But the author of The Rum Diary was then, despite his virtuosic talent for the picturesque threat and brutal insult, the same as that of the Fear and Loathing books in name only. The young man in Puerto Rico was one still beholden to his literary heroes and still speaking in their voices—in his fiction, anyway. Years earlier, while still "Airman Thompson" of the Air Force (and sports editor of his base's newspaper), he wrote letters in the style of H.L. Mencken and harbored dreams of being "universally hailed as the new [Grantland] 'Granny' Rice." Later, while he had a "plum" job as a copyboy at Time, he would type The Great Gatsby and A Farewell to Arms in their entirety in order to study their sentence structures. (Ralph Ellison was also known to copy entire stories from Hemingway for the same reason. The two writers shared this, and an editor: Jim Silberman of Random House was famously Thompson's editor for Fear and Loathing in Las Vegas, and Ellison's for his essay collection, Shadow and Act. Their similarities, beyond Thompson's early penchant for sloe gin, end there.)

A Southerner first, he was in thrall to Faulkner, and he thought that William Styron's Lie Down in Darkness (1951) was "without a doubt the finest book written in this country since the Second World War." He kept the first line of Joseph Conrad's preface to his 1897 novella, The Nigger of the "Narcissus," as a personal mantra while writing in Puerto Rico: "A work that aspires, however humbly, to the condition of art should carry its justification in every line." Thompson, to his credit, never lost this deep, abiding respect for the seriousness of his chosen craft no matter how many peyote buttons he would eat or vehicle floor mats he soaked in raw ether. (It's the fumes that get you.) Even so, The Rum Diary reads, from where we sit at the far side of his singular journalistic career, like someone fighting with the—writerly! not hallucinatory!—voices in his head, all sound and fury.

Listen: "We paid our bill and went out to Sala's car. The top was down and it was a fine, fast ride along the Boulevard to Condado." (So Hemingway right now!) "Most people who deal in words don't have much faith in them and I am no exception—especially the big ones like Happy and Love and Honest and Strong. They are too elusive and far too relative when you compare them to sharp, mean little words like Punk and Cheap and Phony." (Mr. Mencken, take a bow!) And from the novel's final page, try not to imagine a green light beckoning somewhere off in the distance: "Down on the waterfront I could hear the slow clang of a ship's bell as it eased against the pier, and somewhere in the city a motorcycle roared through the narrow streets, sending its echo up the hill to Calle O'Leary." (And goodnight, Mr. Fitzgerald!)

Sure, the novel does reveal flashes of the writer we know—especially his talent for the sweeping flourish of wicked sociological description: "To go to a cocktail party in San Juan was to see all that was cheap and greedy in human nature. What passed for society was a loud, giddy whirl of thieves and pretentious hustlers, a dull sideshow full of quacks and clowns and philistines with gimp mentalities. It was a new wave of Okies, heading south instead of west, and in San Juan they were kingfish because they had literally taken over." It's just that Thompson had yet to resolve the genius of American "letters" that he already was with the delinquent schoolboy in the cord jacket and repp tie who belonged to the Louisville Athenaeum Literary Society.

Thompson's wish for The Rum Diary was not necessarily that it would become the Great American Novel. No, he "merely" wanted it to be the "Great Puerto Rican Novel," (his words!) and he spent the next few years—mostly at Big Sur, California—vainly attempting to finish it. But something—everything—changed once Thompson managed to sell his first piece to a national magazine called Rogue, the "first really valid indication that I might actually make a living at this goddamn writing." With the novel stalled at various publishers in New York, Thompson took off for a year to South America where he wrote (mainly for the National Observer) about politics, culture, and to "find out what it [South America] meant."

It was a transformative experience that saw him return as not merely a writer—he was already that—but instead, "himself"—self-possessed, confident, and no longer a cipher of influence. "After a year of roaming around down here the main thing I've learned is that I now understand the United States and why it will never be what it could have been, or at least tried to be." He was far from the young idealist that hopped a smuggler's boat bound for Colombia; instead, he was one that, on the day that John F. Kennedy was assassinated, wrote a letter to his friend William Kennedy (reputedly the first instance of his use of the phrase "fear and loathing") that could sound like this, and really mean it:

Fiction is dead. Mailer is an antique curiosity. The stakes are now too high and the time too short. What, O what, does Eudora Welty have to say? Fuck that crowd. The only hope now is to swing hard with the right hand, while hanging onto sanity with the left. Politics will become a cockfight and reason will go by the boards. There will have to be somebody to carry the flag.

Fiction, at least as classically defined, was not for him. What Thompson found with what we'll call his "Fear and Loathing" voice was not something that was "truer" than fiction, but rather a truer manner of expression—that didn't necessarily rely on the truth. (Whether that voice eventually shackled his writing to a caricature he might have left behind is a tale for another time.) He didn't know it then, but Hunter had it all figured out in a letter to a fellow aspiring writer, way back before The Rum Diary was even a glint in his eye:

So the difference, I think, boils down to this: you can either impose yourself on reality and > then write about it, or you can impose yourself on reality > by writing.

It's time to go now: I have to go down to the Village and destroy some furniture.

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